1-Iodopentane → 1-(Diphenylmethyl)-3-(pentyloxy)azetidine

HRID 82937

反応式

HRID 82937 の反応式
[C:1]1([CH:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC([O-])(C)C.[K+].I[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>C1COCC1.O>[C:13]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:11][CH:10]([O:12][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:9]2)[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

6

反応物 3

HCID 123351-IodopentaneHCID 3304481-(Diphenylmethyl)azetidin-3-olHCID 23665647Potassium tert-butoxide

生成物 1

HCID 671545431-(Diphenylmethyl)-3-(pentyloxy)azetidine収率 69%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 1-diphenylmethylazetidin-3-ol (300 mg, 1.25 mmol) in THF (4.5 mL) was cooled to 0° C. t-BuOK (1M in THF, 3.75 mL) was added dropwise and the reaction mixture was stirred at room temperature for 1 h then cooled to 0° C. 1-Iodopentane (816 μL, 6.25 mmol) was added and the solution was stirred at room temperature for 18 h. The reaction mixture was diluted with H2O and extracted twice with EtOAc. The organic layers were combined, dried over Na2SO4 and concentrated to dryness. The residue was purified on column chromatography (eluent: pentane/EtOAc, 95/5) to give the title compound (267 mg, 69%) as a clear oil.

後処理

  1. additionwas added dropwise
  2. temperaturethen cooled to 0° C
  3. stirringthe solution was stirred at room temperature for 18 h
  4. extractionextracted twice with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness
  7. customThe residue was purified on column chromatography (eluent: pentane/EtOAc, 95/5)

出典と根拠

ORDレコード
ord-35b2cff55e0f4482aa43c358dd7db91b
出典データセット
uspto-grants-2014_09
特許番号
US08846711B2

関連ノート

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